A Proposal (You're Crazy But I'm In Love With You Anyway)
by KittyNebula
Summary: AU FIC. Felicity Smoak is driven to the edge of her sanity by her boss, CEO of Queen Consolidated and Starlings most desired bachelor Oliver Queen. When he's threatened with deportation for an expired visa Felicity agrees to marry him in exchange for her dream job in IT. Throw in a surprise visit with her family and Felicity starts to see a side to Oliver she never thought existed
1. Chapter 1

**AUTHORS NOTE:**

OK so this was a prompt from Tumblr felicityremarkablesmoak wanted The Proposal only with an Olicity twist. Well I hope this is what you wanted ma lovely * shuffles feet nervously * any feedback is always appreciated. Oh and much as I would like to say they are mine, they aren't neither is The Proposal.

Chapter One

Felicity glanced at the clock, she had ten minutes maybe twenty until her calm was shattered and she had to deal with the onslaught that was her working day. She was just loading up the meeting list for the day when a messenger window popped up on her screen,

_**Sara Lance**__: Adonis is in the building..._

_**Sara Lance**__: and damn that man is fiiiiiiiiiiine_

_**Sara Lance:**__ like tie me to the bed and keep me there at your mercy until Christmas fine!_

_**Felicity Smoak**__: OK, I get it, and do I need to remind you these conversations are stored on the QC servers?_

_**Sara Lance**__: :p party pooper, but Lis you have to admit he's one fine specimen of maledom, I don't know how you can work with him everyday and not think he's hot._

_**Felicity Smoak**__: I am not having this conversation with you Sara I'm kinda busy, lunch?_

_**Sara Lance**__: fine we will continue this later, ping me when you're heading down to the 18th floor ;)_

Felicity rolled her eyes and got to her feet, grabbing the coffee cup from her desk and heading toward the executive elevator to await the arrival of her boss, the one and only Oliver Queen.

If anyone had told her three years ago that she would be Executive Assistant to the CEO of one of the subsidiaries of Queen Consolidated she would have laughed in their face. This had not been part of her life plan, which her mother reminded her of frequently and loudly. She had graduated from MIT at the top of her class and always imagined she would end up in charge of the IT department, instead here she was assisting one Oliver Queen, playboy millionaire and general pain in her ass, and all because in a rash moment she had helped rescue him from one of his recently ex girlfriends.

There had been many occasions since _The Event_ as she referred to it that she had regretted saving him; all be it accidentally from the screeching harpy that had decided to go bat shit crazy after being dumped by him.

_~Flashback~_

"_Listen I'm sorry Bella-"_

_The redhead glared at Oliver, "It's AMANDA!"_

"_Amanda, sweetheart, it was fun, but it was never going to be anything more than that."_

_Felicity watched the drama unfolding before her as she made her way towards the bank of elevators, she'd only been working at QC for six months but she had heard all the stories about the current CEO. She'd have to be stupid not to have realised he was a player just from the few things she had personally witnessed, let alone the gossip blogs online that always had the latest scandal or kiss and tell stories about him. There was no denying he was a very attractive man though, he had the killer combo of sexy smile and naughty twinkle in his eye that had women flocking around him, but she wasn't stupid, blonde yes, stupid no. Oliver Queen was the kind of man her Dad had warned her about before she left for the City._

_She was almost at the elevators when she was unexpectedly shoved sideways. Her reaction was immediate, her self defence training kicked in and she grabbed her attacker and used their momentum to throw them to the floor and pin them. It was only when she became aware of the ripple of applause spreading through the atrium as she sat straddling her attacker that she realised it was the redhead that had been shouting at Oliver. _

_Security had descended from several directions and scrambling to her feet she felt her cheeks burn with embarrassment over her actions, brushing herself off and adjusting her glasses she was about to make her getaway when a warm hand grabbed hers stopping her from running away._

"_Hey that was pretty impressive Ms?"_

_Felicity took deep breath,__** OK not affected by that smile, just give him your name and go back to the safety of IT,**__ "Smoak, Felicity Smoak, I work in IT, I am so sorry about that, I hope I didn't hurt your friend, she just surprised me and I reacted...oh god please don't fire me!"_

_Oliver laughed as he watched the blonde in front of him studiously avoid looking at him while she babbled, he still had a hold of her hand and he was disappointed when she slid it from his grasp, she was adorable in a geeky nerdy kind of way._

"_Well Felicity, you don't have to worry you aren't being fired, in fact I owe you my thanks, I have to say those are some very interesting moves you have there."_

"_Oh... umm, thanks. My dad made me take classes before I moved here."_

"_Wise man, well I have a meeting, so I need to go, but it was a pleasure meeting you Ms. Smoak, I hope we'll meet again."_

_He took her hand again, brushing a kiss across her knuckles and winking at her before he made his way to the Executive Elevator. _

_~End Flashback~_

Sighing she watched the elevator doors, knowing she had only a few moments more before he arrived. If only she had been late that morning three and a half years ago, she would never have registered on his radar, he would also not have appeared repeatedly in IT asking for her to fix his computer, let alone promoting her to his executive assistant not six months later, and despite what people said about her behind her back she had _not_ slept with him. He had flirted and charmed her with bottles of expensive red wine, but he had never made a move on her. She didn't know whether to be flattered or insulted by that.

Her musings were interrupted by the doors of the elevator sliding open to reveal her boss in all his glory, she would never admit it to anyone but her therapist but Sara was right the man was gorgeous. He was as always closely followed by his bodyguard Diggle.

"Good Morning Oliver, your coffee."

At his insistence, when it was only the two of them along with Diggle in the office he asked that she called him Oliver, she was still not entirely comfortable with it but at the end of the day he was her boss so she did as she was told.

"Good Morning and thank you Felicity."

She followed him toward his office reeling off the agenda for the board meeting, he nodded and settled behind his desk. "You need to call legal apparently your immigration lawyer has been trying to get a hold of you but you haven't returned his calls." She peered at him over the top of her glasses, and he gave her one of his 'playboy smiles' as she and Diggle had called them, most women would melt at the mere sight of it but Felicity was immune by now having had to deal with Oliver for so long.

"That might work on Cynthia in accounting but you should know by now it doesn't work with me. Please call legal this morning, now, do you need anything else Oliver?"

"No thank you Felicity, did you have the flowers sent over to Rochelle?"

She tried not to roll her eyes, "Of course, one dozen red roses with the usual, thanks for a wonderful evening note."

"What would I do without you Felicity?"

"Double book yourself probably."

Oliver laughed as he picked up his phone and started to dial, "Well I hope I never have to find out."

Felicity made her way back to her desk followed by Diggle as was their normal morning routine,

"So how are you this morning Digg?"

"I'm fine Felicity, but how was your date last night?"

"Well, he was nice enough but there was no spark, so I doubt we'll go out again." she shrugged not really upset at how things had turned out with Barry, she was too busy organising Olivers love life to worry about her own too much.

"Oh well, I guess we can't all have Oliver's talent with the ladies."

Felicity snorted making Diggle chuckle, "You say that like its a bad thing Digg, trust me as a woman its a very good thing not all guys are like him."

They chatted away about this and that while she filled him in on Olivers schedule for the day, including his lunch date with Nancy and his dinner with Rochelle. They had become friends over the duration of her time working for Oliver, and she felt like Diggle was the big brother she'd never had. He often joined her and Sara for lunch or a coffee and she had to admire the way he refused to confirm or deny many of Olivers exploits to Sara. He also made sure to check out any of her dates if things looked like they were getting serious, but it had been several months since he'd had to give any of her dates the 'you hurt Felicity, I'll break your kneecaps' talk. Eventually they parted ways to go about their mornings.

Felicity was busy preparing a presentation for Oliver when she heard the pitter pat of heels across the floor, looking up she saw Sara's sister Laurel heading toward her. She felt her heart sink into her stomach as she had a feeling the next half an hour was going to end really badly.

Oliver had first seen Laurel when she had come by to visit Sara. They had come to ask Felicity to join them for coffee, he of course had appeared by Felicitys desk, charmed the pant suit off Laurel in almost record time, and they had started a rather intense fling. Laurel was convinced he was in love with her, but Felicity knew better and was waiting for Oliver to grow bored and end it, the fact he was sending roses to the girl he had seen last night was a pretty good indicator that Laurels days were numbered where Oliver was concerned. Felicity could only hope he was gentle about it, as she didn't relish the thought of trying to stop Sara from giving him a piece of her mind.

"Oh hey Laurel, what can I do for you?"

"Is Ollie busy I need to speak to him." Felicity cringed at the nickname, but pretended to check his diary.

"No he has fifteen minutes until his next meeting, go on in."

It took only five for Laurel to emerge from Olivers office in floods of tears. Felicity rolled her eyes, sighing as she hurried over to Laurel and guided her toward the ladies toilet. Some days, especially days like today she cursed the day she had ever heard the name Oliver Queen.

This had not been in the job description of Executive Assistant. In fact this was only one in a long line of things that really hadn't been in her job description, she thought as she passed the still sobbing girl another tissue.

Nowhere had it been listed that consoling the latest ditched conquest of her playboy asshole of a boss was part of her job, and yet here she was.

"But he said what we had was special!"

Felicity scoffed, not realising until Laurel looked at her through her still copious tears that she hadn't kept it internal. "I'm sure he did Laurel."

She wasn't sure if the rubbing on the back was helping, but, after countless episodes of broken hearted, sobbing ex girlfriends of Oliver's she was a pro at consoling distraught women. Fortunately Laurel was the first one she knew personally and she fervently hoped she would be the last, most of Olivers exes she had absolutely nothing in common with and didn't know apart from date notes in Oliver's diary. He had her keep his diary so he didn't double book himself, because of course that would never do, unless they were bikini models in which case it was entirely appropriate and the more the merrier.

"Can I get you anything Laurel?"

The sobbing had died down to sniffling now so Felicity was hopeful she could get Laurel out of the vicinity of Oliver before he could do any more damage.

"N...no I'm fine, I think I'll go home."

"OK, would you like me to call Sara for you?"

Laurel shook her head, "No she'll just say I told you so, I'll just go home."

After fixing her make up and taking a couple of deep breaths Laurel exited the bathroom and headed for the elevator while Felicity went back to her desk and pulled up her messenger service.

**Felicity Smoak: **_Hey, just thought I should warn you, Oliver just dumped Laurel_

**Sara Lance:**_ Crap! Is she OK? Do I need to come up there and give him what for?_

**Felicity Smoak:**_ No I made sure she was alright by the time she left, she said she was going to go home._

**Sara Lance:**_ Thanks Lis, I owe you one, can we rain check on lunch I'll go see her and make sure she's not sobbing into a pint of Ben and Jerrys._

**Felicity Smoak:**_ Sure I have to finish this presentation and finish up the proposal for the Anadac Merger before the meeting this afternoon anyway so I'll work through lunch._

**Sara Lance:**_ Well make sure you eat._

**Felicity Smoak: **_I will, speak to you later!_

Returning her attention to the presentation she'd been working on she lost herself in details. She was half way through the file on the Anadac merger when she became aware of Oliver hovering in the doorway behind her.

"Do you need something Oliver?" She turned in her chair to look at him, still angry with him over the incident with Laurel earlier.

"Are you OK Felicity you seem a little tense?"

"I'm fine, apart from being cried on. Again." She rubbed her temples to ease the tension headache she could feel forming, and as she glanced back at Oliver she saw a flash of something pass over his face but it was gone in the blink of an eye and he carried on as if she hadn't mentioned the incident earlier.

"I need you to do me a favour, Walter has asked me to stop by his office, something about paperwork that he needs from me, can you come and save me in about ten minutes? You know how he can go on sometimes."

"Honestly he's not that bad, but yes, I will call down for you in ten minutes."

"Felicity, that won't work, you know he'll just keep talking, so just come down and get me in ten minutes."

"But I have-"

He cut her off as he entered the elevator "I'll buy you coffee and a Danish from Enchantress on the corner."

She glared at the closing doors muttering under her breath about inconsiderate bosses and their bribery with caffeinated beverages as she saved her work and prepared to once again go save Oliver Queen.

TBC...


	2. Chapter 2

**A/N: first off apologies that its taken me so long to update, real life, Christmas and a fickle muse have not helped.**

**Secondly, I got a couple of PM's from peeps concerned with the fact that Oliver is out of character and not as he is in the show. Althought this is an AU there are reasons why Oliver was written the way he was in Chapter One (some of them are explained in this chapter) please trust me that by the end of my tale Oliver and Felicity will be as they should be.**

**Thirdly and by no means lastly, I just want to say a MASSIVE thanks to everyone thats taken the time to read, comment, follow, favourite and bookmark this - you guys are quite frankly amazeballs!**

**So now I have probably written an authors note thats longer than the chapter itself lets get on with it - Enjoy!**

"I'll buy you coffee and a Danish from Enchantress on the corner." He didn't miss the way her eyes narrowed slightly as the elevator doors closed and he allowed himself a small chuckle at her ire with him. He really shouldn't bait her so much considering he was one of the few people he felt he could truly trust.

Selecting the number of Walters floor he allowed himself to relax for a moment, the playboy CEO façade dropping away to allow him to be the real Oliver if only for a few moments. He wasn't sure when he had realised that by playing up to his playboy persona he could achieve certain things far more easily than by being his real self. It had been a valuable tool when he was making his mark as CEO of this branch of QC especially when people under estimated him.

He may have dropped out of multiple Ivy League colleges and played the party scene like a pro, but he had learned at the side of one of the best businessmen around – his father. He still felt a dull ache in his chest when he thought of his father and his death almost five years ago. Although his death had been a tragic accident, Oliver still felt guilty that he wasn't on the Queens Gambit when it was caught in a bad storm and sunk with no survivors. He was meant to go but then he and Tommy had gotten themselves arrested and while his mother was bailing them out his father had left without him and never come home.

His mother had made him have therapy when he seemed to be in full on self destruct mode, he'd fought her at first, but when he had woken up unable to remember an entire week due to the mixture of alcohol and drugs he'd consumed he acquiesced to her wishes and went to see Doctor Palmer. It had felt uncomfortable at first talking to a stranger who he felt sure was judging him or leaking his sessions to the ever present paparazzi that followed him everywhere, but gradually it started to help him make sense of the way he was feeling guilt for his fathers death.

When he had accepted the position here in Canada he had asked Doctor Palmer to recommend someone that he could continue his sessions with and he had recommend Dr Grace. He had been seeing her on a weekly basis ever since and she was on his list of the few people he could be himself around.

He watched the last couple of floor numbers flash up and plastered on his playboy face again just as the elevator doors opened.

"Oliver!"

Turning at the sound of his name, he saw the very man he was here to see approaching him, and a genuine smile tugged his lips, "Walter, good to see you, Felicity said you needed to see me about something fairly urgent?"

"Good to see you to Oliver, how've you been?" Walter took the hand Oliver offered and they shared a handshake. Walter had been a friend of his fathers and had known him since he was a young boy, he split his time between the Toronto office and the Starling City office assisting both Oliver and his mother as Head of the Legal Department.

"Very well thanks Walter, you?" Walter guided them to his office,"Fine thank you, now it's been bought to my attention that we're missing some paperwork pertaining to your resident visa."

Felicity continued working on the presentation for a good twenty minutes before she decided to do as Oliver asked and go down to Walters office to rescue him. She was still annoyed with him but the lure of coffee was too good to pass up especially the coffee from Enchantress. Saving all her hard work she locked her PC and headed for the elevator, humming to herself as the doors closed.

The ride down to Walters floor was quick and she made her way towards his office, stopping by his secretary first.

"Hi Julie, is Oliver still in with Walter?" she smiled at the redhead who was one of the few people who didn't assume Felicity was sleeping with Oliver.

"Hi Felicity, yes they're still in their meeting, has he sent you to come rescue him again?" Julie laughed, she had worked for Walter long enough to know that if he became involved in explaining something legal he could get a little carried away with himself.

"I'm guessing I'll be alright to interrupt them?" nodding, Julie smiled at Felicity as she raised her hand to knock on the door. Walters muffled voice gave permission for her to open the door and walk in.

Oliver was looking slightly frazzled so Felicity took that as her cue to begin her rescue attempt. "Sorry to interrupt your meeting Mr Queen but I have Mr Johann waiting in your office to discuss the merger plans."

Oliver had moved across the room to stand by Felicity, almost a little to close for her comfort level, she may have been wise to his playboy habits but it didn't change the fact that Oliver Queen was a gorgeous man and she was not as immune to his charms as she would have liked "Thanks Felicity, and it's OK you can call me Oliver, Walter knows." with that cryptic statement he shot her a look as he took her hand lacing their fingers together.

"Congratulations Felicity, I know Olivers father would have loved you and he would be so happy for the pair of you." Felicity was still trying to grasp the fact that Oliver Queen was currently holding her hand in front of one of his fathers oldest friends as said friend leaned into giver her a peck on the cheek, his comment finally registering with her. "Congratulations? I-" Oliver squeezed her hand and she was momentarily distracted by the though of how large his hand felt wrapped around her much smaller one. Using her distraction to his advantage, Oliver had escorted her from Walters office and back into the elevator before she could blink.

She managed to wait until the doors were shut before she rounded on him, "Oliver what the hell is going on?"

He shot her his patented lazy smile, "We're getting married."

TBC


End file.
